2. Why is it that, when I send private messages, some of them are filed in my Sent Items folder and some are filed in my Outbox. Are the Outbox messages actually sent? If not, how can I send and/or delete them?

KAW and KAGU are indeed two different people. If memory serves, husband and wife at this point. I have met them both, they are both awesome people.

Outbox is messages you have sent, but the receiver has not yet read. Sent are messages the receiver has read. I do not know if Outbox messages can be unsent, but if it appears in the outbox, the message is in the receiver's inbox and is awaiting them to read it.